Best Things to Do in Key West in June (2023)

June is an amazing time to visit Key West. But what are the best things to do?


First off, let’s talk about weather. June is the sweet spot month. It’s past the cooler winter months and before the really hot summer months. Average temperatures are in the upper 80’s with the lows not usually falling below 80 degrees(Fahrenheit).

The best part is only about 7 days of rain for the month. But, don’t fret if you find yourself in town on a rainy day. Still lots and lots of stuff to do.

Rainy Day Activities in Key West

What to Wear

Well, we know that the dress code in Key West is…. casual. That’s why we love it so much, right? Plan to pack light. Bring shorts, tee shirts, or tank tops for comfort during the day. A fun sundress or tropical shirt and shorts for dinner and sunset. Bring flip-flops or sandals and comfy walking shoes to enjoy a morning walk. I think the best time to take a walk is early morning. Grab a cup of coffee and stroll down Duval Street. It’s peaceful and quiet.

More ideas on what to wear and what to pack for Key West

What to Do

Walk around and enjoy the tropical flowers. Did you know the Royal Poinciana trees will be in full bloom during June and July? Look for the beautiful red to orange flowers. Also, mangoes are ripe and ready to pick… which is why we have the Fruit (Mango) Festival this time of year.

June is Pride Month. Key West has an amazing celebration each year. It’s one of the best places to celebrate, Pride, Mangoes, and anything else!

Key West Pride – June 7 – 11

Presented by the Key West Business Guild, events showcase the diversity and welcoming atmosphere that makes the southernmost city a top vacation destination for LGBTQ visitors. The festival schedule typically includes pool parties at guesthouses and emporiums, drag shows by Key West’s top performers, nighttime soirees at local clubs, a burlesque-style show with an LGBTQ flair, and the lively “Rainbow Roast.”

But, that’s not all that is happening…

Monday & Tuesday Evening GLOW Hours at Hugh’s Rooftop – through October 24, 2023

The Studios of Key West’s Hugh’s Rooftop offers the best views in town and an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings from 6 to 8 p.m. The bar is open, admission is free. Capacity is limited, so come early. 533 Eaton Street.

Key West Art & Historical Society: Out of the Box – The Art of the Cigar Label– Through October, 22, 2023

The Key West Art & Historical Society presents “Out of the Box: The Art of the Cigar Label.” The exhibition offers a compelling sampling and interpretation of 19th and early 20th century inner and outer cigar labels, showcasing more than 40 lithographs related to the Key West and Cuba cigar manufacturers. From the 1880s into the early 20th century, cigar manufacturers desired an avenue to market their particular cigars to consumers. Mass production of cigars in Cuba and Florida contributed to the successes of lithographic arts. Included with museum general admission. Custom House Museum, 281 Front Street, 10 a.m. to 5 p.m. daily.

Shakedown on the Green – Key West Island Market – June 3

All are welcome the first Saturday of every month for Shakedown on the Green: Key West Island Market, located on the Sunset Green Lawn at 24 North Hotel, 3820 N. Roosevelt. This family-friendly, Key West Island Market features local goods, artists, food trucks and more. Free admission and free parking. $5 mimosas available.

Waterfront Playhouse – Hedwig and the Angry Itch – June 7 – 10, 2023

The award winning musical about Hedwig Robinson, a genderqueer East German singer of a fictional rock and roll band. A musical you will never forget!

Sunset Green: Na Ma Sit & Stay Yoga with Your Dog – June 11

The Keys Collection offers Na Ma Sit & Stay Yoga with Your Dog the second Sunday of each month at 9:30 am. at the Sunset Green event lawn in Key West. Admission is free but a $10 donation is suggested, with all proceeds donated to Florida Keys SPCA. Bring your dog and your own mat. Located at 3820 N. Roosevelt Blvd. between The Gates and 24 North hotels.

10th Annual VFW Fishing Tournament – June 16-18, 2023

A family fun tournament, cash prizes are to be awarded for the heaviest catch of five target species — mahi-mahi (dolphin fish), wahoo, tuna, snapper and grouper. Cash prizes are awarded for the heaviest catches of each including a first-place prize of 5 thousand dollars for the heaviest mahi-mahi. A “super prize” of either 20 thousand dollars or a new Toyota Corolla is to be awarded to the angler who catches the heaviest dolphin fish of 50 pounds or over. Captains and anglers can choose to fish either Saturday or Sunday, but not both. All proceeds benefit disabled and needy veterans of Monroe County. The opening captains meeting and final awards banquet will be held at VFW Post 3911, 2200 N. Roosevelt Blvd.


Embark on an adventurous swim – a 12.5 loop around the island with fantastic landscape views of Key West and swimming in the pristine waters. Compete in different categories of either a solo swimmer, solo swimmers with fins, a solo swimmer using a mermaid tail or a monofin or gather your friends and compete in the relay category of a 2-person, 3-person, 4-person, 5-person, or 6-person teams. Not interested in the full island swim? Try some of the smaller races offered, a 6.1-mile swim, a 2-mile swim, a 1-mile swim, or an 800-yard swim.

Seventh Annual Mango Fest Key West – June 22 – 25, 2023

Experience all things mango through culinary treats, education and demonstrations during this celebration of the Keys’ sweet indigenous fruit and its heritage. Stroll around the Mango Mania vendor village, enter a photo contest, enjoy mouthwatering mango-themed specialties prepared by top local chefs and much more. The festival is presented by the Key West Police Athletic League and supports its local youth programs.

Sunset Green: Live at Sunset Concert

The Keys Collection presents the “Live at Sunset” free monthly concert series on the last Tuesday of every month on the Sunset Green! The lawn opens at 6 p.m., with local talent performing from 7-10 p.m. Free entry and parking, food & drinks for purchase. Located at 3820 N. Roosevelt Blvd. between The Gates and 24 North hotels.

Key West Key Lime Festival – June 30 – July 4, 2023

Key West’s annual Key Lime Festival is set to celebrate the world’s most sensational citrus with a bountiful array of festivities across the island where Key lime pie was conceived. Over five days, lovers of the lime can indulge in a full menu of activities, from an event kick-off cookbook signing and champagne reception with festival co-founder and “Key West Key Lime Pie Cookbook” author David Sloan; delicious Key lime-centric dinner and brunch events; a wild and world famous Key lime pie eating contest; a gravity-defying Key lime pie drop competition – from the top of the Key West Lighthouse; a Key lime pie hop, and for those with a taste for limey libations, a Key lime rum tasting and a bar Sip & Stroll. There’s much more, including numerous family-friendly activities.

What’s Happening Up the Keys

History of Diving Museum: Aquanauts to Astronauts Exhibit – Through December 31, 2023

The Aquanauts to Astronauts exhibit focuses on the fascinating relationship between diving and space travel, how NASA uses diving to train future astronauts, and the incredible people who have both been to space and visited the bottom of the sea. The exhibit includes artifacts from NASA. The museum is located at 82990 Overseas Highway bayside.

No matter when you visit Key West, you will have a great time. Not looking for an organized event? Just want to relax, enjoy the tropical vibes, a gorgeous sunset? The month of June is still an amazing time to visit. Spend time at Smather’s Beach, or simply enjoy some live music on Duval.

Why is Smather’s Beach the Best?

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